3-(Bromomethyl)benzoic acid → 3-(Fluoromethyl)benzoic acid

HRID 980463Notes

Reaction equation

HRID 980463 reaction equation
[F-:1].[K+].Br[CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]>C(#N)C>[F:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 2456503-(Bromomethyl)benzoic acidHCID 522689Potassium Fluoride

Product 1

HCID 202215213-(Fluoromethyl)benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.945 g (11.15 millimoles) of 1,4,7,10,13,16-hexanona-cyclooctadecane (18-Crown-6) are dissolved in 30 ml anhydrous acetonitrile, whereupon 6.48 g (111.54 millimoles) of anhydrous potassium fluoride are added. The mixture is stirred for half an hour and 12 g (55.77 millimoles) of 3-bromomethyl benzoic acid are added. The reaction mixture is stirred at 50° C. for 3 hours, whereupon it is filtered and the filtrate is evaporated in vacuo. The residue is taken up in 100 ml of ethyl acetate and the suspension is washed with 15 ml of water, 15 ml of a saturated sodium chloride solution, dried over sodium sulfate, filtered and the organic solvent is distilled off in vacuo. Thus 7.3 g of the title compound are obtained, yield 85%.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at 50° C. for 3 hours, whereupon it
  3. filtrationis filtered
  4. customthe filtrate is evaporated in vacuo
  5. washthe suspension is washed with 15 ml of water, 15 ml of a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. distillationthe organic solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-9c604f55c44044f095d9043b10761c4f
Source dataset
uspto-grants-1987_01
Patent number
US04638002

Reaction notes

Loading…